CA2350137C - Nouveaux composes de piperazine et de piperidine - Google Patents

Nouveaux composes de piperazine et de piperidine Download PDF

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Publication number
CA2350137C
CA2350137C CA002350137A CA2350137A CA2350137C CA 2350137 C CA2350137 C CA 2350137C CA 002350137 A CA002350137 A CA 002350137A CA 2350137 A CA2350137 A CA 2350137A CA 2350137 C CA2350137 C CA 2350137C
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CA
Canada
Prior art keywords
compound
prodrug
salt
composition
treatment
Prior art date
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Expired - Fee Related
Application number
CA002350137A
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English (en)
Other versions
CA2350137A1 (fr
Inventor
Roelof W. Feenstra
Johannes A. M. Van Der Heijden
Johannes Mos
Stephen K. Long
Gerben M. Visser
Cornelis G. Kruse
Gustaaf J. M. Van Scharrenburg
Anne G. Toorop
Gerrit Toorop (Deceased)
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Duphar International Research BV
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Duphar International Research BV
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Application filed by Duphar International Research BV filed Critical Duphar International Research BV
Publication of CA2350137A1 publication Critical patent/CA2350137A1/fr
Application granted granted Critical
Publication of CA2350137C publication Critical patent/CA2350137C/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne un nouveau groupe de dérivés de pipérazine et de pipéridine représentés par la formule (I), des sels et des promédicaments de ceux-ci. Dans cette formule, S1 représente hydrogène, halogène, (1-3C)alkyle, CN, CF3, OCF3, SCF3, (1-3C)alkoxy, amino ou mono- ou (1-3C)dialkylamino substitué, ou hydroxy, X représente NR3, S, CH2, O, SO ou SO2, où R3 représente H ou (1-3C)alkyle, .......Z représente =C ouN, R1 et R2 représentent indépendamment H ou (1-3C)alkyle, ou R1 et R2 peuvent former ensemble un pont de 2 ou 3 C-atomes, R4 représente hydrogène ou (1-3C)alkyle, Q représente méthyle, éthyle, éthyle substitué par un ou plusieurs atomes de fluorine, cyclopropyl méthyle, éventuellement substitué par un ou plusieurs atomes de fluorine . On a découvert que ces composés sont à la fois partiellement agonistes du récepteur D2 de la dopamine et des activités induites par un agoniste partiel du récepteur 5-HT1A de la sérotonine
CA002350137A 1998-11-13 1999-11-10 Nouveaux composes de piperazine et de piperidine Expired - Fee Related CA2350137C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP98203871 1998-11-13
EP98203871.3 1998-11-13
PCT/EP1999/008702 WO2000029397A1 (fr) 1998-11-13 1999-11-10 Nouveaux composes de piperazine et de piperidine

Publications (2)

Publication Number Publication Date
CA2350137A1 CA2350137A1 (fr) 2000-05-25
CA2350137C true CA2350137C (fr) 2008-04-22

Family

ID=8234340

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002350137A Expired - Fee Related CA2350137C (fr) 1998-11-13 1999-11-10 Nouveaux composes de piperazine et de piperidine

Country Status (27)

Country Link
US (1) US6780864B1 (fr)
EP (1) EP1131308B1 (fr)
JP (1) JP3638874B2 (fr)
KR (1) KR100619465B1 (fr)
CN (1) CN1225462C (fr)
AR (1) AR021256A1 (fr)
AT (1) ATE267183T1 (fr)
AU (1) AU756470B2 (fr)
BR (1) BR9915293B1 (fr)
CA (1) CA2350137C (fr)
CZ (1) CZ299774B6 (fr)
DE (1) DE69917478T2 (fr)
DK (1) DK1131308T3 (fr)
DZ (1) DZ2934A1 (fr)
ES (1) ES2217833T3 (fr)
HU (1) HUP0104922A3 (fr)
IL (2) IL143028A0 (fr)
MX (1) MXPA01004854A (fr)
NO (1) NO318888B1 (fr)
NZ (1) NZ511584A (fr)
PL (1) PL193685B1 (fr)
RU (1) RU2225406C2 (fr)
SI (1) SI1131308T1 (fr)
SK (1) SK285648B6 (fr)
TW (1) TWI252230B (fr)
UA (1) UA71590C2 (fr)
WO (1) WO2000029397A1 (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA73981C2 (en) 2000-03-10 2005-10-17 Merck Patent Gmbh (r)-(-)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]-chromane for treatment of extrapyramidal movement disorders (variants), pharmaceutical composition and kit
US20030186838A1 (en) * 2000-05-12 2003-10-02 Feenstra Roelof W. Use of compounds having combined dopamine d2, 5-ht1a and alpha adrenoreceptor agonistic action for treating cns disorders
EP1283838B1 (fr) * 2000-05-12 2003-12-03 Solvay Pharmaceuticals B.V. Composes de piperazine et piperidine
RU2283648C2 (ru) * 2000-11-14 2006-09-20 Мерк Патент Гмбх Новое применение комбинированных селективных антагонистов допаминового рецептора d2 и агонистов рецептора 5-нт 1a
AR034206A1 (es) * 2001-02-16 2004-02-04 Solvay Pharm Bv Un procedimiento para la preparacion de mesilatos de derivados de piperazina y dichos mesilatos
US6800648B2 (en) * 2001-04-26 2004-10-05 Wyeth Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-1,6,9-trioxa-3-AZA-cyclopenta[a]naphthalen-2-one
US6743796B2 (en) 2001-05-07 2004-06-01 Wyeth Piperazinyl-isatins
ES2323451T7 (es) 2001-07-20 2011-08-01 Psychogenics Inc. Tratamiento para el trastorno de hiperactividad con deficit de atencion.
PT1408964E (pt) 2001-07-26 2007-05-31 Merck Patent Gmbh Utilização de 2-5-(4-fluorofenil) -3-piridilmetilaminometil-cromano e de seus sais fisiologicamente aceitáveis.
EP1336406A1 (fr) * 2002-02-14 2003-08-20 Solvay Pharmaceuticals B.V. Agonistes partiels du récepteur D2 de la dopamine et inhibiteurs de la sérotonine et/ou de la noradrénaline
WO2004000837A1 (fr) * 2002-06-25 2003-12-31 Sumitomo Pharmaceuticals Co., Ltd. Nouveau derive de benzoxazolinone
US7435738B2 (en) 2003-08-18 2008-10-14 Solvay Pharmaceuticals, Inc. Stable crystalline form of bifeprunox mesylate (7-[4-([1,1′-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone monomethanesulfonate)
EP1595542A1 (fr) * 2004-03-26 2005-11-16 Solvay Pharmaceuticals B.V. Administration iontophoretique de composés piperazinyl-2(3h)-benzoxazoloniques
US7596407B2 (en) 2004-03-26 2009-09-29 Solvay Pharmaceuticals, B.V. Transdermal iontophoretic delivery of piperazinyl-2(3H)-benzoxazolone compounds
JP4914346B2 (ja) * 2004-05-27 2012-04-11 ユセベ ファルマ ソシエテ アノニム ベンズオキサゾロン誘導体、その調製方法及びその使用
US7405216B2 (en) 2004-08-18 2008-07-29 Solvay Pharmaceuticals, B.V. Stable crystalline form of bifeprunox mesylate (7-[4-([1,1′-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone monomethanesulfonate)
US7964604B2 (en) 2005-02-18 2011-06-21 Solvay Pharmaceuticals B.V. Bifeprunox mesylate maintenance dose compositions and methods for using the same
US7423040B2 (en) 2005-02-18 2008-09-09 Irene Eijgendaal Stable crystalline form of bifeprunox mesylate, dosage forms thereof and methods for using same
US7750013B2 (en) 2005-08-22 2010-07-06 Solvay Pharmaceuticals, B.V. N-oxides as prodrugs of piperazine and piperidine derivatives
ATE417834T1 (de) * 2005-08-22 2009-01-15 Solvay Pharm Bv N-oxide als prodrugs von piperazin- und piperidinderivaten
AR058022A1 (es) * 2005-08-22 2008-01-23 Solvay Pharm Bv Derivados de benzooxazoles, composiciones farmaceuticas y su uso para el tratamiento de desordenes del sistema nervioso.
US7786126B2 (en) 2006-06-16 2010-08-31 Solvay Pharmaceuticals B.V. Combination preparations comprising SLV308 and a dopamine agonist
US8106056B2 (en) 2006-06-16 2012-01-31 Solvay Pharmaceuticals B.V. Combination preparations comprising bifeprunox and a dopamine agonist
UY32935A (es) * 2009-10-12 2011-05-31 Abbott Healthcare Products Bv Polimorfos de pardoprunox
US11103499B2 (en) 2016-08-26 2021-08-31 EXCIVA (UG) (haftungsbeschränkt) Compositions and methods thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2567884B1 (fr) * 1984-07-19 1987-03-06 Roussel Uclaf Nouveaux derives de l'indole, leur preparation, leur application comme medicaments et les compositions les renfermant
EP0189612B1 (fr) * 1984-12-21 1992-11-04 Duphar International Research B.V Médicaments à activité psychotrope
EP0190472B1 (fr) * 1984-12-21 1989-07-12 Duphar International Research B.V Médicaments à activité antipsychotique
DK148392D0 (da) * 1992-12-09 1992-12-09 Lundbeck & Co As H Heterocykliske forbindelser
ZA954689B (en) 1994-06-08 1996-01-29 Lundbeck & Co As H 4-Aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzothiophenemethyl) piperidines tetrahydropyridines or piperazines
FI970310L (fi) * 1994-07-26 1997-01-24 Pfizer 4-indolijohdannaiset serotoniinin vaikuttaja- ja vastavaikuttaja-aineina
JP3989554B2 (ja) * 1996-03-29 2007-10-10 デユフアー・インターナシヨナル・リサーチ・ベー・ブイ ピペラジンおよびピペリジン化合物
EP0900792B1 (fr) 1997-09-02 2003-10-29 Duphar International Research B.V Dérivés de pipéridine et de pipérazine comme agonistes du récepteur 5-HT1

Also Published As

Publication number Publication date
UA71590C2 (en) 2004-12-15
RU2225406C2 (ru) 2004-03-10
AU756470B2 (en) 2003-01-16
IL143028A (en) 2006-12-10
HUP0104922A3 (en) 2003-05-28
CZ20011657A3 (cs) 2001-10-17
CA2350137A1 (fr) 2000-05-25
SK285648B6 (sk) 2007-05-03
CZ299774B6 (cs) 2008-11-19
SI1131308T1 (en) 2004-10-31
KR100619465B1 (ko) 2006-09-05
NO20012339D0 (no) 2001-05-11
ATE267183T1 (de) 2004-06-15
MXPA01004854A (es) 2005-07-25
DE69917478D1 (de) 2004-06-24
KR20010080995A (ko) 2001-08-25
HK1039489A1 (en) 2002-04-26
BR9915293B1 (pt) 2011-11-01
DE69917478T2 (de) 2004-09-16
US6780864B1 (en) 2004-08-24
NZ511584A (en) 2003-01-31
WO2000029397A1 (fr) 2000-05-25
NO318888B1 (no) 2005-05-18
TWI252230B (en) 2006-04-01
DZ2934A1 (fr) 2004-03-15
CN1378540A (zh) 2002-11-06
PL193685B1 (pl) 2007-03-30
CN1225462C (zh) 2005-11-02
ES2217833T3 (es) 2004-11-01
EP1131308B1 (fr) 2004-05-19
HUP0104922A2 (en) 2002-08-28
NO20012339L (no) 2001-05-11
IL143028A0 (en) 2002-04-21
DK1131308T3 (da) 2004-06-28
EP1131308A1 (fr) 2001-09-12
SK6492001A3 (en) 2001-10-08
BR9915293A (pt) 2001-08-07
AR021256A1 (es) 2002-07-03
AU1270900A (en) 2000-06-05
PL347635A1 (en) 2002-04-22
JP3638874B2 (ja) 2005-04-13
JP2002530276A (ja) 2002-09-17

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